scholarly journals Studies on the Chemical Diversities of Secondary Metabolites Produced by Neosartorya fischeri via the OSMAC Method

Molecules ◽  
2018 ◽  
Vol 23 (11) ◽  
pp. 2772 ◽  
Author(s):  
You-Min Ying ◽  
Lu Huang ◽  
Ting Tian ◽  
Cui-Yu Li ◽  
Shi-Lei Wang ◽  
...  
Keyword(s):  
Secondary Metabolites ◽  
Cancer Cell Line ◽  
2D Nmr ◽  
Natural Occurrence ◽  
Fungal Metabolites ◽  
Isolation And Identification ◽  
Late Step ◽  
Neosartorya Fischeri ◽  
The One ◽  
First Time

The One Strain Many Compounds (OSMAC) method was applied to explore the chemical diversities of secondary metabolites produced by Neosartorya fischeri NRRL 181. Four pyripyropenes 1–4, eight steroids 5–11, and four prenylated indole alkaloids 12–15, were obtained from the fungus cultured in petri dishes containing potato dextrose agar (PDA). 1,7,11-trideacetylpyripyropene A (1) and 1,11-dideacetyl pyripyropene A (2) were obtained and spectroscopically characterized (1D, 2D NMR, and HR-ESI-MS) from a natural source for the first time. It offered a sustainable source of these two compounds, which were usually used as starting materials in preparing pyripyropene derivatives. In addition, as compared with all the other naturally occurring pyripyropenes, 1 and 2 possessed unique acetylation patterns that did not follow the established late-step biosynthetic rules of pyripyropenes. The natural occurrence of 1 and 2 in the fungus implied that the timing and order of hydroxylation and acetylation in the late-step biosynthetic pathway of pyripyropenes remained to be revealed. The isolation and identification of 1–15 indicated that the OSMAC method could remarkably alter the metabolic profile and enrich the chemical diversities of fungal metabolites. Compounds 1–4 exhibited no obvious cytotoxicity against the triple-negative breast cancer cell line MDA-MB-231 as compared with taxol.

scholarly journals Neuroprotective Metabolites from Vietnamese Marine Derived Fungi of Aspergillus and Penicillium Genera

Marine Drugs ◽  
2020 ◽  
Vol 18 (12) ◽  
pp. 608
Author(s):  
Elena V. Girich ◽  
Anton N. Yurchenko ◽  
Olga F. Smetanina ◽  
Phan Thi Hoai Trinh ◽  
Ngo Thi Duy Ngoc ◽  
...  
Keyword(s):  
Molecular Weight ◽  
Secondary Metabolites ◽  
Cell Viability ◽  
Chemical Structure ◽  
Aspergillus Terreus ◽  
Marine Fungi ◽  
2D Nmr ◽  
Natural Source ◽  
Low Molecular Weight ◽  
First Time

Low molecular weight secondary metabolites of marine fungi Aspergillus flocculosus, Aspergillus terreus and Penicillium sp. from Van Phong and Nha Trang Bays (Vietnam) were studied and a number of polyketides, bis-indole quinones and terpenoids were isolated. The structures of the isolated compounds were determined by 1D and 2D NMR and HR-ESI-MS techniques. Stereochemistry of some compounds was established based on ECD data. A chemical structure of asterriquinone F (6) was thoroughly described for the first time. Anthraquinone (13) was firstly obtained from a natural source. Neuroprotective influences of the isolated compounds against 6-OHDA, paraquat and rotenone toxicity were investigated. 4-Hydroxyscytalone (1), 4-hydroxy-6-dehydroxyscytalone (2) and demethylcitreoviranol (3) have shown significant increasing of paraquat- and rotenone-treated Neuro-2a cell viability and anti-ROS activity.

scholarly journals Anticancer Activities of Chemical Constituents from Leaves and Twigs of Mitrephora winitii

2021 ◽  
Vol 21 (3) ◽  
pp. 699
Author(s):  
Sukee Sukdee ◽  
Puttinan Meepowpan ◽  
Narong Nantasaen ◽  
Siriporn Jungsuttiwong ◽  
Sarinya Hadsadee ◽  
...  
Keyword(s):  
Cancer Cell ◽  
Chemical Constituents ◽  
Cancer Cell Line ◽  
2D Nmr ◽  
Anticancer Activities ◽  
Chromatographic Separations ◽  
Chemical Structures ◽  
Anti Cancer ◽  
First Time ◽  
Mcf 7

The genus Mitrephora has been investigated and its anti-inflammatory, anti-bacterial and anti-parasitical activities were examined along with its potential as an anti-cancer cell line and inhibitor for platelet aggregation. In this work, air-dried leaves and twigs of M. winitii were grounded and extracted with n-hexane, ethyl acetate and methanol, respectively. Chromatographic separations of these extracts led to the isolation of three known compounds and one new compound (compound 2). The chemical structures of these were identified using spectroscopic investigation of 1D- and 2D-NMR and the resulting data confirmed these as stigmasterol (1), (3,4-dimethoxyphenyl)(5-(3,4-dimethoxyphenyl)-4-(hydroxymethyl)tetrahydrofuran-3-yl)methanol (2), diayangambin (3), and methyl-L-inositol (4). The chemical constituents were reported the first time in M. winitii. Compound 2 showed anti-cancer cell lines with ED50 13.07 µg/mL against KB cells and then was tested for cytotoxicity against MCF-7 cells with ED50 11.77 µg/mL.

scholarly journals Antimicrobial Secondary Metabolites from the Seawater-Derived Fungus Aspergillus sydowii SW9

Molecules ◽  
2019 ◽  
Vol 24 (24) ◽  
pp. 4596 ◽  
Author(s):  
Yu-Jing Liu ◽  
Jian-Long Zhang ◽  
Chen Li ◽  
Xue-Gen Mu ◽  
Xiao-Li Liu ◽  
...  
Keyword(s):  
Secondary Metabolites ◽  
Pathogenic Bacteria ◽  
2D Nmr ◽  
Aspergillus Sydowii ◽  
Isolation And Identification ◽  
Spectrometric Data ◽  
Lead Compounds ◽  
Acid Analogue ◽  
Chorismic Acid ◽  
Quantum Chemical Computations

Marine-derived fungi are considered to be valuable producers of bioactive secondary metabolites used as lead compounds with medicinal importance. In this study, chemical investigation of the seawater-derived fungus Aspergillus sydowii SW9 led to the isolation and identification of one new quinazolinone alkaloid, 2-(4-hydroxybenzyl)-4-(3-acetyl)quinazolin-one (1), one new aromatic bisabolene-type sesquiterpenoid, (2) and one new chorismic acid analogue (3), as well as two known alkaloids (compounds 4 and 5). Their structures were determined by extensive 1D/2D NMR and mass spectrometric data, and the absolute configurations of 2 and 3 were assigned by the analysis of ECD spectra aided by quantum chemical computations. Compounds 1, 2, and 4 exhibited selective inhibitory activities against the human pathogenic bacteria Escherichia coli, Staphylococcus aureus, S. epidermidis, and Streptococcus pneumoniae, with MIC values ranging from 2.0 to 16 μg/mL.

scholarly journals Flavonoids from Lonchocarpus muehlbergianus

2004 ◽  
Vol 76 (4) ◽  
pp. 651-661 ◽  
Author(s):  
Aderbal F. Magalhães ◽  
Ana M.G.A. Tozzi ◽  
Eva G. Magalhães ◽  
Ivani S. Blanco ◽  
Maria-Del-Pilar C. Soriano
Keyword(s):  
Quantitative Analysis ◽  
Spectral Data ◽  
13C Nmr ◽  
2D Nmr ◽  
Reversed Phase ◽  
Light Petroleum ◽  
Natural Occurrence ◽  
Reversed Phase Hplc ◽  
First Time

The light petroleum extract from the roots of Lonchocarpus muehlbergianus Hassl contained nine flavonoids, including six new ones. These are 2,4-cis-2,4,5,8-tetramethoxy-(2´´,3´´:6,7)-furanoflavan; 2,4-cis-4-hydroxy-2,5,8-trimethoxy-(2´´,3´´:6,7)-furanoflavan; 2,4-cis-2-prenyloxy-4,5,8-trimethoxy-(2´´,3´´:6,7)-fu-ranoflavan; 2,4-cis-2-prenyloxy-4-hydroxy-5,8-dimethoxy-(2´´,3´´:6,7)-furanoflavan; 2',5',6'-trimethoxy-9-(1,1-dimethylallyoxy)-[2´´,3´´:3´,4´]-furanochalcone; 5,6-dimethoxy-(2´´,3´´:7,8)-furanoflavone, identi-fied by analysis of their spectral data (UV, IR, ¹H and 13C NMR, 2D-NMR, NOE and MS). The natural occurrence of 2,4-dioxygenated flavan derivatives is being reported for the first time. Quantitative analysis of the petrol extract, by using reversed-phase HPLC, showed that the most abundant flavonoid in the extract is 2,4-cis-2,4,5,8- tetramethoxy-(2´´,3´´:6,7)-furanoflavan.

scholarly journals Isolation and Identification of the Five Novel Flavonoids from Genipa americana Leaves

Molecules ◽  
2018 ◽  
Vol 23 (10) ◽  
pp. 2521 ◽  
Author(s):  
Larissa Silva ◽  
Jovelina Alves ◽  
Emerson da Silva Siqueira ◽  
Manoel de Souza Neto ◽  
Lucas Abreu ◽  
...  
Keyword(s):  
Secondary Metabolites ◽  
Medicinal Plant ◽  
Ethyl Acetate ◽  
Folk Medicine ◽  
Ethyl Acetate Fraction ◽  
Spectroscopic Methods ◽  
Isolation And Identification ◽  
1H And 13C Nmr ◽  
Chemical Structures ◽  
First Time

Genipa americana is a medicinal plant popularly known as “jenipapo”, which occurs in Brazil and belongs to the Rubiaceae family. It is a species widely distributed in the tropical Central and South America, especially in the Cerrado biome. Their leaves and fruits are used as food and popularly in folk medicine to treat anemias, as an antidiarrheal, and anti-syphilitic. Iridoids are the main secondary metabolites described from G. americana, but few studies have been conducted with their leaves. In this study, the aim was to chemical approach for identify the main compounds present at the extract of G. americana leaves. The powdered leaves were extracted by maceration with EtOH: water (70:30, v/v), following liquid-liquid partition with petroleum ether, chloroform, ethyl acetate and n-butanol. A total of 13 compounds were identified. In addition three flavonoids were isolated from the ethyl acetate fraction: quercetin-3-O-robinoside (GAF 1), kaempferol-3-O-robinoside (GAF 2) and isorhamnetin-3-O-robinoside (GAF 3) and, from n-butanol fraction more two flavonoids were isolated, kaempferol-3-O-robinoside-7-O-rhamnoside (robinin) (GAF 4) and isorhamnetin-3-O-robinoside-7-rhamnoside (GAF 5). Chemical structures of these five flavonoids were elucidated using spectroscopic methods (MS, 1H and 13C-NMR 1D and 2D). These flavonoids glycosides were described for the first time in G. americana.

scholarly journals A New Colchicinoid from Colchicum tauri, an Unexplored Meadow Saffron Native to Jordan

2006 ◽  
Vol 1 (2) ◽  
pp. 1934578X0600100 ◽  
Author(s):  
Feras Q. Alali ◽  
Amani S. Ma'aya'h ◽  
Ahmad Alkofahi ◽  
Amjad Qandil ◽  
Chen Li ◽  
...  
Keyword(s):  
Brine Shrimp ◽  
2D Nmr ◽  
Biological Evaluation ◽  
Preparative Hplc ◽  
Low Resolution ◽  
Isolation And Identification ◽  
Brine Shrimp Lethality ◽  
Chromatographic Techniques ◽  
General Toxicity ◽  
First Time

This study reports the isolation, characterization, and biological evaluation of constituents of Colchicum tauri Siehe ex Stef. (Colchicaceae), an unexplored Colchicum species native to Jordan. Methanolic extraction, crude alkaloid fractionation, and separation using several different chromatographic techniques (open columns, preparative TLC, and semi-preparative HPLC), as directed by the brine shrimp lethality test (BST), resulted in the isolation and identification of nine compounds: (-)-colchicine (1), (-)-2-demethylcolchicine (2), (-)-3-demethylcolchicine (3), (-)-demecolcine (4), (-)- N-methyldemecolcine (5), (-)-3-demethyl- N-methyldemecolcine (6), β-lumicolchicine (7), 3-demethyl-β-lumicolchicine (8), and apigenin (9). Compounds 1–5 and 7–8 were isolated for the first time from this species, while compound (6) represents a new colchicinoid. The structure elucidations were achieved using a series of spectroscopic and spectrometric techniques, principally 1D-NMR (1H, and 13C), 2D-NMR (COSY, ROESY, HMBC, and HSQC), and low resolution EI-MS. All compounds were tested for general toxicity using the BST, and compounds 1 and 4 were found to be the most potent, with LC50 values of 2.5 and 8.1 μg/mL, respectively.

scholarly journals Chemical Constituents of Cichorium intybus and their Inhibitory Effects against Urease and α-Chymotrypsin Enzymes

2011 ◽  
Vol 6 (8) ◽  
pp. 1934578X1100600
Author(s):  
Sumayya Saied ◽  
Shazia Shah ◽  
Zulfiqar Ali ◽  
Ajmal Khan ◽  
Bishnu P. Marasini ◽  
...  
Keyword(s):  
Chemical Constituents ◽  
2D Nmr ◽  
Cichorium Intybus ◽  
Spectroscopic Techniques ◽  
Inhibitory Effects ◽  
Isolation And Identification ◽  
Aerial Parts ◽  
Phytochemical Investigation ◽  
Hydroxyphenylacetic Acid ◽  
First Time

Phytochemical investigation of the aerial parts of Cichorium intybus L. resulted in the isolation and identification of two new natural metabolites, 2,6-di[but-3( E)-en-2-onyl]naphthalene (1), and 3,3′,4,4′-tetrahydroxychalcone (2), along with nine known compounds. Their structures were determined by spectroscopic techniques including 1D and 2D NMR. The known compounds were identified as scopoletin (3), 4-hydroxyphenylacetic acid (4), 3-hydroxy-4-methoxybenzoic acid (5), 4,4′-dihydroxychalcone (6), 6,7-dihydroxycoumarine (7), 1-triacontanol (8), lupeol (9), β-sitosterol (10), and β-sitosterol-3- O-β-glucopyranoside (11). Compounds 4-6 and 8 are reported for the first time from C. intybus. Compounds 2 and 3 showed weak inhibitory activities against urease and α-chymotrypsin enzymes, respectively.

scholarly journals Isolation and identification of secondary metabolites of Umbilicaria crustulosa (Ach.) Frey

2016 ◽  
Vol 14 (2) ◽  
pp. 125-133 ◽  
Author(s):  
Ivana Zlatanovic ◽  
Goran Petrovic ◽  
Olga Jovanovic ◽  
Ivana Zrnzevic ◽  
Gordana Stojanovic
Keyword(s):  
Secondary Metabolites ◽  
Methyl Esters ◽  
2D Nmr ◽  
Ethyl Esters ◽  
Preparative Hplc ◽  
Isolation And Identification ◽  
Significant Difference ◽  
Chemical Profiles ◽  
Ethanol Extracts ◽  
Gyrophoric Acid

Herein, we have studied secondary metabolites of Umbilicaria crustulosa (Ach.) Frey. By using preparative HPLC, four compounds were isolated from the U. crustulosa methanol extract. The structure of isolated lichen substances was determined on the basis of their 1H, 13C and 2D NMR spectra as follows: methyl orsellinate, lecanoric acid, methyl lecanorate and gyrophoric acid. In addition to methanol, the composition of acetone and ethanol extracts were also studied (analytical HPLC). Relative distributions (%) of the detected constituents were as follows (in methanol/acetone/ethanol extracts): methyl orsellinate (5.7/1.5/0.9), lecanoric acid (17.9/5.7/6.7), crustinic acid (8.0/2.8/2.5), methyl lecanorate (4.8/0/0) and gyrophoric acid (59.2/78.0/85.7). A significant difference in the chemical profiles of the studied extracts was in the presence/absence of methyl esters of lichen acids. Nonetheless, the chemical composition of the ethanol extracts (no ethyl esters were detected) and the fact that treatment of acetone and ethanol extracts with methanol does not lead to changes in their composition suggests that methyl esters were not artifacts of the isolation procedure. The lower content of methyl orsellinate and the absence of methyl lecanorate from acetone and ethanol extracts may be the result of different solubilities of these compounds in methanol, ethanol and acetone.

Chemical Constituents of Adesmia Boronioides and Evaluation of their Antioxidant Activity

2015 ◽  
Vol 8 (3) ◽  
pp. 2919-2223
Author(s):  
Orlando Muñoz ◽  
C Delporte
Keyword(s):  
Chemical Constituents ◽  
Antioxidant Properties ◽  
2D Nmr ◽  
Isolation And Identification ◽  
Ongoing Research ◽  
Phytochemical Investigation ◽  
Kaempferol Glycoside ◽  
Pharmacologically Active ◽  
Pharmacologically Active Compounds ◽  
First Time

As part of our ongoing research into the pharmacologically active compounds of Chilean flora, here we did phytochemical investigation of Adesmia boronioides Hook.f (fabaceae). (Papilonaceae) leaves. This effort has led to isolation and identification of liqueritigenin, isoliquiritigenin, sesamin, isodrimenin and a kaempferol glycoside, kaempferol 3-O-β-D-[galactopyranosyl  (1–2) rhamnoside]-7-O –α-L-rhamnopyranoside.Compound structures were identified by 1D- and 2D-NMR experiments, mass and UV spectrometry and comparison with data from the literature. This is the first time these compounds have been isolated from this plant’s leaves.These active constituents have been studied further pharmacologically. Antioxidant properties in A. boronioides leaves were determined.

scholarly journals A New Chromene Isolated from Ageratum conyzoides

2011 ◽  
Vol 6 (9) ◽  
pp. 1934578X1100600 ◽  
Author(s):  
Abiodun Humphrey Adebayo ◽  
Chang-Jiu Ji ◽  
Yu-Mei Zhang ◽  
Wen-Jun He ◽  
Guang-Zhi Zeng ◽  
...  
Keyword(s):  
Cell Line ◽  
Cancer Cell ◽  
Inhibitory Activity ◽  
Cancer Cell Line ◽  
Ethanol Extract ◽  
2D Nmr ◽  
Ageratum Conyzoides ◽  
2D Nmr Spectroscopy ◽  
Whole Plant ◽  
First Time

From the ethanol extract of the whole plant of Ageratum conyzoides L. (Compositae), one new chromene, 2,2-dimethylchromene 7-methoxy-6- O-β-D-glucopyranoside, was isolated, together with thirteen known compounds, seven of which were being reported for the first time. The compounds were all characterized by MS, IR, 1D- and 2D-NMR spectroscopy. 7,3′,5′-Tri- O-methyltricetin (7), precocene II (9), 3,5,7,4′-tetrahydroxyflavone (13) and 5,6,7,3′,4′,5′-hexamethoxyflavone (14) exhibited inhibitory activity on the P-388 cancer cell line with IC50 values of 12.8, 24.8, 3.5 and 7.8 μM respectively, while compound 9 exhibited inhibitory activity on the HT-29 cancer cell line with an IC50 value of 61μM; the others showed no significant cytotoxic activity on the cell lines tested.

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